Abstract Recent advances in the direct C(sp 2 )─H chalcogenylation of indoles, particularly in C─S and C─Se bond formation, have significantly improved the synthesis of mono‐ and dichalcogenyl indoles, leading to more environmentally friendly approaches. These sulfenylation and selenylation processes contribute to the development of molecules with considerable biological and pharmaceutical potential. Over the past decade, remarkable progress in these methods has highlighted their impact on the field. This review outlines these techniques and their reaction mechanisms, which will be valuable for future research and development.